COMPARATIVE INVESTIGATION OF ORGANIC COMPOUNDS Janine Anne A. Mateo, Cyra Kaye C. Mina, Jose Mari I.

Oconer, William Bernard N. Ong and Althea D. Ouano Group 7 2F Medical Technology Organic Chemistry Laboratory ABSTRACT
Organic compound are the complex compounds of carbon. It can be classified into hydrocarbons and hydrocarbon derivatives based on the substituent element or group of highest priority to the hydrocarbon. In this experiment, comparative investigation was done to differentiate the properties of organic compounds. Intrinsic characteristics were observed, solubility of the samples were tested, reaction of the litmus paper on the samples were noted, and ignition test was done to determine the flammability and luminosity of the samples. Gathered information shows that organic compounds do have different characteristics from each other.

INTRODUCTION
Organic compound is any compound of carbon with covalent bonding related to the living organisms present in nature. Most of the organic compounds are non polar and hence are bad conductors of heat and electricity. Some organic compounds get ionized when dissolved in water or subjected to electrolysis due to the polar substituents but the main end product will be non-polar carbon dioxide.[1] Because carbon atoms bond to one another easily, the basis of most organic compounds is comprised of carbon chains that vary in length and shape. Hydrogen, nitrogen, and oxygen atoms are the most common atoms that are generally attached to the carbon atoms. Each carbon atom has 4 number of valence which increases the complexity of the compounds that are formed. Since carbon atoms are able to create double and triple bond with other atoms or to itself, it further raises the likehood for variation in the molecular make-up of organic compounds.[2] Organic compounds can be classified as hydrocarbons and hydrocarbon derivatives on the basis of their hydrogen replacements by other elements or by other group of elements (functional group). All hydrocarbons are insoluble in water because of their relatively non-polar characteristic and they can be easily distributed. There are two large classes of hydrocarbon, namely: saturated and unsaturated hydrocarbons. Saturated hydrocarbons are the simplest type of organic compounds in which all carbon-carbon bonds are single bonds and thus contain the maximum possible number of hydrogen per carbon. An example of a saturated hydrocarbon is an alkane because it lacks bond.[3] On the other hand, alkenes and alkynes that have fewer hydrogen per carbon than related alkenes are referred to as unsaturated.

Organic compounds may have similar physical properties but differ on their chemical properties. The physical state of an organic compound at room temperature may indicate the strength of interactive forces that exist between its molecules.[4] Solubility involves a)the formation of one layer, if the compounds are miscible, or b) formation of two layers, if the compounds are immiscible. The solubility of organic compounds can be divided into two major categories: solubility in which a chemical reaction is the driving force and solubility in which simple miscibility is the only mechanism involved, such as dissolving ethyl ether (CH3CH2OCH2CH3) in carbon tetrachloride (CCl4). [3] Flammability determines the degree of a material or a substance that will sustain combustion. This can be tested by doing the ignition test. Some organic compounds decompose and blacken, while others burst into flames.[4] Lastly, infrared (IR) spectrometry is the absorption measurement of different IR frequencies by a sample positioned in the path of an IR beam.[5] The main goal of IR spectroscopic analysis is to determine the chemical functional groups in the sample. Different functional groups absorb characteristic frequencies of IR radiation.[6] The objective of this experiment is to make a distinction among the properties of some organic compounds through their (1) intrinsic physical properties, (2) solubility in different solvents, (3) flammability, and (4) infrared spectra of their functional groups.

EXPERIMENTAL
A. Samples Used Cyclohexane, DCM, Ethanol, Phenol, Acid, Ethyl Acetate, and Ethylamine Benzoic

B. Procedure 1. PHYSICAL STATE, COLOR AND ODOR The physical state of all the samples that was used was examined, the color

was recorded, and the odor was taken determined through a wafting motion. 2. SOLUBILITY PROPERTIES Four drops of liquid and 0.1g of solid samples, which was ground in order to have a high surface area, were placed into a clean and dry test tube. The solvent was added in a dropwise manner by using a dry calibrated dropper. The number of drops was also recorded until it reached 3 mL. The mixture was not heated. Then, changes in color, and warming or effervescence were noted. The samples was then described based on the amount of solvent added as very soluble, soluble, slightly soluble, or insoluble. On the other hand, the solubility of liquid samples was described as miscible, slightly miscible, or immiscible. 3. REACTION WITH LITMUS PAPER The aqueous solution of the samples, that were soluble in water, was tested with red and blue litmus paper. Color changes in both litmus papers were noted. 4. IGNITION TEST 3-5 drops of liquid sample and a pinch amount of solid sample were placed in a small evaporating dish and ignited with a match. Then, the samples were observed if they were flammable or not and the color of the flame was also indicated. All the results were noted. DCM CH2Cl2 Liquid Colorless Paste -like

Ethanol

Liquid

Colorless

Alcoh ol

Phenol

Liquid

Red Orange

Paste -like

Benzoic Acid

Solid

White

Odorl ess

Ethyl Acetate

Liquid

Colorless

Plasti c ballo on

Liquid Ethyla mine

Colorless

Amm onia

Table 1. Intrinsic properties of the samples

RESULTS AND DISCUSSION

The following tables show all the observations that were gathered throughout the experiment: A. OBSERVATIONS OF PHYSICAL STATE, COLOR AND ODOR

Sample

Condense d Structural Formula

Physi cal State at RT

Color

Odor

Table 1 shows that all the samples are in liquid state at room temperature except for benzoic acid. Most of the liquid samples are colorless except for phenol because of oxidation. Cyclohexane, DCM, and phenol have a paste-like odor; ethyl acetate has a plastic-balloon odor; ethanol has an odor of an alcohol; benzoic acid is odorless; and ethylamine smells like ammonia because of the presence of amine which is a functional group. B. TESTS FOR SOLUBILITY PROPERTIES Sample In H2O In 5% NaOH solution
Immiscible

Cyclohe xane

Liquid

Colorless

Paste -like

In 5% HCl solution
Immiscible

Cyclohe xane

Immiscible

DCM

Immiscible

Immiscible

Immiscible

Benzoic Acid

Acidic

Ethanol Phenol Benzoic Acid Ethyl Acetate Ethylam ine

Miscible

Miscible

Miscible

Ethyl Acetate Ethylamine

Neutral

Immiscible

Miscible

Immiscible

Basic

Insoluble

Insoluble

Insoluble

Table 3. Acidity, basicity and neutrality of the sample Table 3 shows that phenol and benzoic acid are acidic, ethylamine is basic, ethanol and ethyl acetate are neutral. Cyclohexane and DCM will not have a reaction because they are immiscible. Change in color of the litmus paper indicates the acidity, basicity, and neutrality of a substance. Blue litmus paper to red litmus paper indicates that the substance is acid while red to blue litmus paper indicates that the substance is basic. Retention of color means that the substance is neutral. D. IGNITION TEST Sample Cyclohexane DCM Ethanol Phenol Benzoic Acid Ethyl Acetate Flammability and Color
Flammable (yellow;sooty) Non-flammable Flammable (blue)

Immiscible

Immiscible

Immiscible

Miscible

Miscible

Miscible

Table 2. Solubility properties of the sample Table 2 shows that cyclohexane, DCM, and ethyl acetate are immiscible in all the solvents that were used; DCM and ethylamine are both miscible in the three solvents; benzoic acid is insoluble in the three solvents; and phenol is immiscible in water and 5% HCl solution, and miscible in 5% NaOH solution. The solubility of the samples is related to the polarity of the two substances and the intermolecular forces of attraction during the solution process. Water is a polar solvent and all the samples that are miscible or soluble in it are said to be polar. Solubility of a sample(insoluble in H2O) in NaOH indicates that it has an acidic functional group while samples(soluble in H2O) that are also soluble in HCl shows that it has a basic property. [8] C. REACTION WITH LITMUS PAPER Sample Cyclohexane DCM Ethanol Phenol
Neutral

Non-flammable

Non-flammable

Flammable (yellow)

Reaction with Litmus Paper

Ethylamine

Flammable (yellow)

Table 4. Flammability and color change of the sample Table 4 shows that ethyl acetate, ethylamine, and cyclohexane have a yellow flame while ethanol has a blue flame. DCM, phenol, and benzoic acid are non-flammable. The characteristics of flame are essential in determining the nature of a certain carbon. As

Acidic

the oxygen content of the compound increases, the flame will undergo complete combustion which, in turn, make it clearer resulting to color blue flame(non-luminous). Incomplete combustion is indicated by a yellow flame(luminous) due to the relatively high number of carbons and there will be presence of soot.

REFERENCES
[1] Stoker, H.S. (2011). General, Organic, and Biological Chemistry 6th edition. USA: Brooks/ Cole [2]Smith, J.G. (2008) Organic Chemistry. New York,USA/McGraw-Hill [3] Klein, D. (2012). Organic Chemistry. USA/John Wiley & Sons Inc. [4] Shriner, R., Hermann, C., Morrill, T., Curtin, D., and Fuson, R. (2003). USA/John Wiley & Sons Inc. [5] Lambert, J., Gronert S., Shurvell, H., Lightner, D., and Cooks, R. (2011). Organic Structural Spectroscopy. USA: Prentice Hall [6] Hsu, S. Infrared spectroscopy http://www.prenhall.com/settle/chapters/ch15.p df 6/18/09